Torah Gems: Behar-Bechukotai
Experience the gems of the Parsha with the classic commentaries, and a kabbalstic twist.
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Why would anyone, especially a Jew sell himself into slavery? Isn't it bad enough that the Jews served as slave to the Egyptians?
Well, Anonymous, it wasn't ever anyone's option A. Slavery is definitely not the best way to go.
As you pointed out, we were freed from slavery in Egypt, in theory never to be slaves again.
That is why a voluntary slave who extends the length of his slavery to the yovel gets his ear pierced. The Talmud explains that it is as if to say "the ear that heard me say that you will only be slaves to me, never to another human, and still voluntarily chose slavery shall be pierced" (Kiddushin 22b).
So why would anyone choose slavery?
Well, because they needed the money. When a Jew bought a slave, he was legally bound to support the slave's family as well. So a man that felt like he had no other way to prevent his family from starving might choose slavery.